Triamine stabilized adhesive compositions



United States Patent 3,231,403 TRIAMINE STABILIZED ADHESIVE COMPOSITIONS Edward B. Hodge and Grant J. Lalferty, Terre Haute, 1135., assignors to Commercial Solvents Corporation, New York, N.Y., a corporation of Maryland No Drawing. Filed May 17, 1962, Ser. No. 195,374 11 Claims. (Cl. 106-135) Our invention relates to adhesive compositions. More particularly our invention relates to adhesive compositions stabilized against attack by microorganisms.

Adhesive compositions are made from a wide variety of materials and have many and varied applications. Generally most adhesives are separated into three main categories: those which are of an animal origin such as the animal glues, the fish glues, and the casein pastes; those of vegetable origin such as the gums, the starch a hesives, the dextrin adhesives, the rubber latex adhesives, and the natural resin adhesives; and the synthetic adhesives such as the synthetic resins, for example, those of the urea-formaldehyde, phenol-formaldehyde, acrylic, andv vinyl types... All such adhesives possess one commom-property, the ability to enable surfaces to merge on contact or under pressure and after merger, resist separation;

A common problem of adhesive compositions is their lack of resistance to attack by certain microorganisms during storage. On certain of the widely used types of adhesives, particularly casein adhesives and starch adhesives, spoilage takes place in a matter of days. Such spoilage, which can finally cause coagulation and even separation of the adhesive, is easily observed by the formation of mold and the production of highly noxious odors.

We have now discovered a means whereby adhesive compositions can be made resistant to spoilage. Our new adhesive compositions even retain this resistance after long storage periods. Thus, our stabilized adhesive compositions are not only eifective in preventing mold formation and noxious odors but successfully inhibit decomposition, coagulation and separation of the adhesive composition itself.

Our adhesive compositions are produced by incorporating a stabilizing amount of a triamine having the following general formula:

R H2 CH3 /R NOCo-N R/ NHz H wherein R is an alkyl radical into the adhesive composition.

Examples of suitable triamines coming within the scope of our invention are l l ,N -bis(2-ethylhexyl)-N -2-dimethyl 1,2,3-propanetriamine, N ,N -bis(l-methylheptyl)-N -2-dimethyl-1,2,3-propanetriamine, N ,N -dibutyl- N -2-dimethyl-l ,2,3-propanetriamine, N ,N -dinouyl-N Z-dimethyl-1,2,3-propanetriamine, etc., and the like.

The amount of triamine necessary to stabilize adhesive compositions will naturally vary depending in the main on the particular adhesive to be stabilized and the conditions of storage. Usually, however, amounts as low as 100 ppm. by weight based on the weight of the adhesive compositions are effective in controlling spoilage. Generally we have found that it is not necessary to exceed 1,000 ppm. of our stabilizing agents in the adhesive compositions. Under most circumstances satisfactory results are obtained when 250 ppm. to 500 ppm. of our stabilizers are utilized.

The following examples further illustrate our invention, but we do not intend to be limited to the procedures, types of adhesives, or amounts of triamines set out therein. In-

3,231,403 Patented Jan. 25, 1966 clusion of all equivalents obvious to the art is intended.

EXAMPLE I To test the effectiveness of our triamines in preserving adhesive compositions, a casein adhesive composition containing 70 grams casein, 7 mls. of a 29% ammonia solution, and 623 mls. of water was divided into 5 equal portions. A triamine stabilizing agent was added to 4 of the 5 portions and the remaining portion was used as a control. Each of the 5 portions was then inoculated with a mold found growing in a casein-adhesive composition. Each of the 5 portions was then placed in a separate open jar and allowed to stand for 30 days. The following table shows the results of the 30-day test.

The procedure of Example I was followed with the exception that a polyvinyl alcohol starch adhesive containing 25 grams polyvinyl alcohol, 70 grams corn starch, and 525 mls. water was utilized instead of the casein adhesive of Example I. The following table shows the results of this test.

Table 11 Amount of Mold Portion Triamine Triamine, Formation ppm.

1 N,NMais(2-ethylhexyD-N 2- 500 None.

dimethyl-l,2,3-propanetriamine. 2 N ,lW-dinouyl-N -2-dimethyl 1,2, 500 Do.

3-propanetriamine. 3 N ,N -dibutyl-N l-dimethyl-l,2, 1,000 Do.

S-propanetriamine. 4 N .N -bis(l-methylheptyl)-N -2- 1,000 Do.

dimethyl-l,2,3-propanetria1nine. 5 Control Covered sample.

EXAMPLE In An adhesive composed of 24 kilograms dextrin, 24

liters of water, and 10 grams of ginger grass oil was effectively stabilized by N ,N -bis(2-ethylhexyl)-N -2-dimethyl-1,2,3-propanetriamine.

EXAMPLE IV A vegetable glue adhesive composition composed of grams of gum arabic, 0.2 grams calcium hydroxide, 300 ml. of water, and 10 grams of aluminum sulfate was effectively stabilized by N ,N -bis( 1-methylheptyl)-N -2- dimethyl-1,2,3-propanetriamine.

EXAMPLE V An adhesive composition composed of 100 grams of glue, 100 mls. of water, 5 grams of glycerin, and 3 grams of potassium bichromate was effectively stabilized by N N -dibutyl-N -2-dimethyl-1,2,3-propanetriamine.

EXAMPLE VI An adhesive composition composed of 17 pounds castor oil, 100 pounds pine resin, and 50 pounds denatured alcohol was effectively stabilized by N ,N -dinonyl- N -2-dimethyl-1,2,3-propanetriamine.

Now having described our invention, what we claim is: 1. An adhesive composition stabilized against microorganism attack which comprises an adhesive and a stabilizing amount of a triamine having the following formula:

R H: CH3 H: R

R/ NH: H

wherein R is alkyl.

2. The composition of claim 1 wherein the adhesive is a casein adhesive.

3. The composition of claim 1 wherein the adhesive is a starch adhesive.

4. The composition of claim 1 wherein the adhesive is a glue adhesive.

5. The composition of claim 1 wherein the adhesive is a rubber latex adhesive.

6. An adhesive composition stabilized against microorganism attack which comprises an adhesive and from about 100 to about 1,000 p.p.m. of a triamine having the following formula:

wherein R is alkyl.

7. An adhesive composition stabilized against micro- A organism attack which comprises an adhesive and from about 250 to about 500 ppm. of a triamine having the following formula:

20 References Cited by the Examiner UNITED STATES PATENTS 1,925,819 9/1933 Putnam et a1. l06-l25 2,244,712 6/ 1941 Kyrides 16722 2,246,524 6/1941 Kyrides 167-22 2,436,779 2/1948 Senkus 260583 2,888,421 5/1959 Adams et a1 260-29] 3,058,835 10/1962 Sheeran 106146 30 ALEXANDER H. BRODMERKEL, Primary Examiner.

MORRIS LIEBMAN, Examiner. 

1. AN ADHESIVE COMPOSITION STABILIZED AGAINST MICROORGANISM ATTACK WHICH COMPRISES AN ADHESIVE AND A STABILIZING AMOUNT OF A TRIAMINE HAVING THE FOLLOWING FORMULA: R-N(-R)-CH2-C(-CH3)(-NH2)-CH2-NH-R WHEREIN R IS ALKYL.
 4. THE COMPOSITION OF CLAIM 1 WHEREIN THE ADHESIVE IS A GLUE ADHESIVE. 